Chiral synthesis of thienamycin from D-glucose

Details Chiral synthesis of thienamycin from D-glucose Chiral synthesis of thienamycin from D-glucose

1984-01-25

1985-10-01

Brust, Joseph Paul

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C11700, C07C12186

Patent

active

045445028

ABSTRACT:
Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R.sup.1 is lower alkyl or aralkyl, such as benzyl and the like; and R.sup.2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

REFERENCES:
patent: 4384998 (1983-05-01), Durette
patent: 4448976 (1984-05-01), Durette

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